I got Lookout as the answer to 17 down (it's the only word that fits) but I'm blowed if I fully understand it. The ruffian is a lout a lookout is a man on board, but then so is K for King in chess. I am absolutely stumped by the "not right" bit. Perhaps Dannyk13 will come to the rescue again.
the man on board (chess, that is) is a rok, less r for rght = ook.
sorry, dannyk13 if this steals your thunder, but no sign of follow up at the moment from you.